Winter Park Homes for Sale

Winter Park Homes for Sale

Winter Park, located in Orange County, Florida, is a charming city known for its picturesque landscapes and vibrant community. With its tree-lined streets, beautiful lakes, and historic architecture, Winter Park offers a unique blend of natural beauty and cultural attractions.

If you're looking for homes for sale in Winter Park, you're in luck. This region boasts a wide range of real estate options to suit every taste and budget. From cozy bungalows to luxurious waterfront properties, Winter Park has something for everyone.

One of the key attractions of Winter Park is its proximity to Orlando, which is just a short drive away. This means residents can enjoy all the excitement and entertainment options that the city has to offer while still enjoying the peaceful and serene atmosphere of Winter Park.

In addition to its natural beauty, Winter Park is also home to a thriving arts and culture scene. The city is known for its numerous art galleries, museums, and theaters, making it a haven for art enthusiasts. The annual Winter Park Sidewalk Art Festival is a highly anticipated event that attracts artists and visitors from all over the country.

For outdoor enthusiasts, Winter Park offers plenty of recreational activities. From boating and fishing on the lakes to exploring the numerous parks and trails, there is no shortage of ways to enjoy the great outdoors.

With its charming atmosphere, rich history, and abundance of amenities, Winter Park is a sought-after destination for homebuyers. Whether you're looking for a permanent residence or a vacation home, Winter Park has the perfect property waiting for you.

Newest Winter Park Homes for Sale

$610,000
3 Beds ⋅ 2 Baths ⋅ Edgewood Sub SubDv. ⋅ 32789 Zip Code
Rare opportunity to own a home in one of Winter Park's most sought-after neighborhoods. This charming 3 bedroom, 2 bathroom home sits on a 52x150 lot and is full of endless potential. Whether you are looking for the perfect starter home or an exceptional investment to build your dream home, this property offers an unbeatable combination of location, lifestyle, and value. The kitchen was beautifully remodeled with white custom cabinetry and gorgeous granite countertops. The oversized lot allows you plenty of room to expand, entertain, or simply just enjoy friends and family around the custom built fire pit. There is a large shed in the backyard to store all of your yard needs. Leave the car behind and enjoy one of Central Florida's most walkable neighborhoods. You are just steps away from East End Market, unique local shops, an incredible dining scene, including several Michelin-recognized restaurants and the top-rated Audubon Park K-8. Zoned for Winter Park High, and minutes to Park Avenue and Rollins College. This desirable pocket of Winter Park offers a true community where neighbors know one another and local events bring them together. This is more than just a home-it's an opportunity to invest in an exceptional lifestyle while making a smart long-term investment in one of Winter Park's most desirable areas. This is one not to miss! Welcome Home!

2719 Woodside Avenue, Winter Park
$1,725,000
4 Beds ⋅ 4 Baths ⋅ Lakeview Terrace SubDv. ⋅ 32789 Zip Code
Welcome to modern luxury in the heart of Winter Park! This custom 2014-built estate rests on an expansive double lot in the highly sought-after Lakeview Terrace community. Offering nearly 3,800 sq. ft. of sophisticated yet comfortable living space, this 4-bedroom, 3.5-bath residence combines timeless architectural details—including soaring vaulted ceilings, crown molding, and dark hardwood floors—with the ultimate layout for functional living. An inviting foyer with volume ceilings and a large transom window fills the home with natural light, leading into a spacious family room anchored by a marble-wrapped electric fireplace with custom lighting and a media niche. The chef’s kitchen is open, bright, and ideal for entertaining, featuring 42-inch shaker double-stacked cabinetry, premium Bosch stainless steel appliances, granite countertops, a designer backsplash, a large pantry, and peninsula bar seating alongside an eat-in breakfast nook. Seamlessly connected, the formal dining room shines with a tray ceiling, custom wallpaper, and designer fixtures. Convenience continues in the oversized laundry room, equipped with a second refrigerator and secondary pantry. Designed for total flexibility, the main level features a dedicated executive office, a media room, a secondary guest suite, and a lavish primary retreat. The primary suite boasts custom built-ins, a massive walk-in closet, direct outdoor access, and a spa-inspired bath with double vanities, a soaking tub, and a large dual-head shower. Upstairs, you’ll find two additional spacious bedrooms, a full bath, and a versatile bonus loft. Outside, a private resort oasis awaits with an open-air lanai and covered porch for alfresco dining, surrounded by lush mature landscaping, pathways trimmed with turf grass, and professional landscape lighting. The heated pool and spa feature a sun shelf with a fountain feature and linear fire elements along the edge that transform the backyard at night. Completing the estate is a 3-car total garage layout, featuring an attached 2-car garage plus a separate detached structure with guest house, studio, or private office potential. Located just one mile from historic Park Avenue, zoned for top-rated schools (Lakemont Elementary, Glenridge Middle, Winter Park High), and walkable to Phelps Park, the YMCA, and local dining.

1840 Bryan Avenue, Winter Park
$354,999
3 Beds ⋅ 2 Baths ⋅ Fairview Heights Rep SubDv. ⋅ 32789 Zip Code
Opportunity awaits in this 3-bedroom, 2-bath concrete block home located in the established Fairview Heights area of Winter Park. Offering 1,344 square feet of living space on a 6,460-square-foot lot, this single-story residence features a functional floor plan with tile flooring throughout the main living and dining areas. A covered rear entry leads to a brick paver patio and a fully fenced backyard with mature trees, providing space for entertaining, pets, or outdoor enjoyment. According to the seller, the roof was replaced approximately 10 years ago and the HVAC system approximately 6 years ago. Buyers are encouraged to verify all information and permits. The property is currently tenant-occupied on a month-to-month lease and may be delivered vacant at closing with a minimum of 30 days' notice, or continue as an investment opportunity. No HOA. Conveniently located near shopping, dining, parks, major roadways.

310 Granada Drive, Winter Park
$655,000
3 Beds ⋅ 3 Baths ⋅ Garden Acres SubDv. ⋅ 32789 Zip Code
It’s so easy to fall in love with this stunning, completely renovated three-bedroom, two-and-a-half-bath home. Over the past five years, the sellers have transformed it into an absolute showstopper with extensive upgrades, including new electrical, updated plumbing, air-conditioning and water heater systems, and fully renovated kitchen and baths to gorgeous modern standards. All windows and doors were also replaced during this period. A quaint sunroom/den overlooks the professionally designed and fully fenced yard, complete with a beautiful pergola, elegant brick pavers and a serene fountain that invites you outdoors, ideal for hosting gatherings or simply enjoying this relaxing private enclave. A beautiful circular brick-paved driveway leads to the attached one-car garage with convenient laundry facilities, an uncommon and desirable feature in a classic bungalow. Zoned for great schools and in one of Winter Park’s sought-after neighborhoods, this property offers strong long-term value appreciation and is within a short distance of Mead Botanical Garden and Seven Oaks Park. Rollins College, Hannibal Square, Park Avenue, and downtown Orlando are all just minutes away, making this a prime location.

913 Camellia Avenue, Winter Park
$1,000,050
4 Beds ⋅ 3 Baths ⋅ Park Pointe Rep SubDv. ⋅ 32789 Zip Code
A MUST SEE BEAUTIFUL WELL MAINTAINED POOL HOME by ORIGINAL OWNERS in SOUGHT AFTER WINTER PARK ZIPCODE & SCHOOLS. PICTURES PROVIDE a GREAT PORTRAYAL of the FLOORPLAN but THERE ARE MANY FEATURES TO POINT OUT - THIS 2868 SQFT HOME has a 3-WAY SPLIT with 4 BEDROOMS, 3 FULL BATHROOMS, plus BONUS ROOM & OFFICE. YOU WILL NOT BELIEVE ALL THE STORAGE, STORAGE, STORAGE UNDER AIR! The BONUS ROOM (12.4 X 11.7) OFF PRIMARY BEDROOM COULD BE a NURSERY, OFFICE, EXERCISE ROOM, or OWNERS RETREAT. There is an ADDITIONAL OFFICE (13.6 X 11.6 ) with BUILT N DESK & STORAGE CABINETS MAKING a GREAT HOMESCHOOL ROOM, CRAFT AREA, or HOME OFFICE WHERE a PRIVATE EXTERIOR ENTRY DOOR is NEEDED. ONE BEDROOM could be USED as an IN-LAW SUITE with IT’S ENSUITE BATHROOM with SHOWER. The SPACIOUS GARAGE has NEW SHARK FLOORING (7/26), NEW PAINT, NEW ELECTRIC CAR CHARGING OUTLET (6/26), NEW INSULATED GARAGE DOOR & A MINI SPLIT AC – LOTS OF POSSIBILITIES! MANY FUN MEMORIES can be ENJOYED with FAMILY & FRIENDS AROUND the BEAUTIFUL SCREENED POOL & LARGE COVERED LANAI & DECK ( RESURFACED 9/25 ) The NEW OWNER of this LOVELY HOME will APPRECIATE all the UPDATES that have BEEN DONE over LAST FEW YEARS – NEW $29K LENOX UPGRADED AC (3/26), NEW FRONT DOOR (4/26), NEW GOOGLE NEST DOORBELL (3/26), NEW INSULATION in ATTIC & ON GARAGE DOOR (6/26), NEW PAVER DRIVEWAY (5/26 ) NEW UPGRADED FLASHING AROUND CHIMNEY (5/26), GAS TANKLESS WATER HEATER W RECIRCULATING FEATURE(2023), NEW DUCT WORK (2019) NEW WINDOWS (2020), WHOLE HOUSE REPLUMBED (2020), ROOF (2016), STAINLESS APPLIANCES (2019), WHOLE HOUSE WATER SOFTNER & DOUBLE OSMOSIS SYSTEM for DRINKING WATER, SELLER WILL CONSIDER CARPET ALLOWANCE WITH ACCEPTABLE OFFER. ****** THIS HOME IS WORTH SEEING ******

2667 Cochise Trail, Winter Park
$449,000
3 Beds ⋅ 2 Baths ⋅ Stansbury Estates SubDv. ⋅ 32789 Zip Code
Tucked away on a quiet street just minutes from the heart of Winter Park, this beautifully updated bungalow offers the perfect blend of character, modern updates, and flexibility. The true standout is the detached 1-bedroom, 1-bath guest house, a rare feature that's ideal for visitors, a private home office, fitness studio, creative space, or even an income-producing opportunity. The main home features two spacious bedrooms and a beautifully renovated bathroom, while timeless charm is showcased throughout with original hardwood floors, crown molding, custom built-ins, and an open-concept living space. The thoughtfully designed kitchen combines butcher block and custom concrete countertops with quality appliances, while the adjacent laundry and utility room adds extra functionality. Step outside to a backyard designed for year-round Florida living. The covered patio, complete with café lighting and ceiling fans, overlooks a fully equipped outdoor kitchen with custom concrete countertops, creating the perfect setting for entertaining. Lush tropical landscaping, an outdoor shower, and abundant storage complete the private outdoor oasis. Beyond its charm, this home is packed with practical upgrades including a metal roof, whole-house natural gas generator, and an exterior security camera system, providing comfort and peace of mind through every season.

2007 Cornell Avenue, Winter Park
$3,199,000
4 Beds ⋅ 5 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
Under Construction. Perfectly positioned along one of Winter Park's most picturesque tree-lined cobblestone streets, this exceptional new construction residence offers a rare opportunity to own a home where timeless architecture, refined craftsmanship, and an unrivaled location come together. A striking marble mosaic foyer creates an unforgettable first impression, immediately setting the tone for the level of detail found throughout the residence. Just off the entry, a dedicated home office provides the ideal space for working remotely or enjoying a quiet retreat. Beyond, the thoughtfully designed floor plan unfolds into expansive living spaces filled with natural light and connected by effortless flow. The great room serves as the heart of the home, highlighted by a custom-built entertainment wall with integrated LED lighting, a sleek electric fireplace, and oversized sliding glass doors that blur the line between indoor and outdoor living. Designed for both everyday living and elegant entertaining, the chef's kitchen is a showpiece. Taj Mahal quartzite countertops are paired with an exceptional suite of Thermador appliances, including a paneled built-in refrigerator, while extensive custom cabinetry provides an abundance of storage without compromising the clean, sophisticated aesthetic. The adjoining dining room creates an inviting setting for gatherings and is complemented by a beautifully appointed dry bar complete with a wine refrigerator, making entertaining effortless. Privately situated on the main level, the primary suite is a true retreat with direct access to the lanai through expansive sliding glass doors. The spa-inspired bath showcases exquisite marble mosaic tile, dual vanities, a freestanding soaking tub, an oversized walk-in shower, and a generous custom walk-in closet, creating a space that feels both luxurious and serene. Upstairs, three spacious guest bedrooms are thoughtfully arranged alongside a comfortable secondary living area and an expansive bonus room, offering remarkable flexibility for a media room, game room, fitness studio, or additional gathering space. The outdoor living experience is equally impressive. A spacious covered lanai is designed for year-round enjoyment, featuring a fully equipped summer kitchen, generous space for alfresco dining and entertaining, a sparkling pool and spa, and ample green space for recreation or relaxation. While the home's finishes and craftsmanship are exceptional, it is the location that truly sets it apart. Enjoy the rare privilege of walking to the boutiques, award-winning restaurants, and vibrant atmosphere of Park Avenue, the campus of Rollins College, Virginia Park, and the acclaimed East End Market. Zoned for highly sought-after Audubon K-8 and surrounded by the charm and character of the Lake Sue District, this is more than a home; it's a statement of luxury Winter Park living.

361 E Kings Way, Winter Park
$635,000
2 Beds ⋅ 2 Baths ⋅ Morseland Sub SubDv. ⋅ 32789 Zip Code
Luxury Meets Timeless Design in the Heart of Winter Park. Welcome to this beautifully renovated 2-bedroom, 2-bath residence where thoughtful design and exceptional craftsmanship come together to create a truly move-in ready home. Located just minutes from the shops and restaurants of Park Avenue, this home offers a rare combination of modern luxury and classic Winter Park charm. The light-filled open floor plan is anchored by a stunning chef's kitchen featuring Taj Mahal quartz countertops, custom cabinetry, premium stainless steel appliances, and a dramatic waterfall island that serves as the centerpiece of the home. Wide-plank wood flooring flows throughout, while recessed lighting, designer fixtures, and carefully selected finishes add warmth and sophistication to every room. The spacious primary suite is designed as a private retreat with custom-built closet systems and a beautifully appointed en-suite bath showcasing dual vanities, designer tile, quartz countertops, and a custom frameless glass shower. The guest bedroom also features custom closet cabinetry and easy access to an equally impressive second bathroom finished with high-end materials and elegant fixtures. From the welcoming covered front porch to the abundance of natural light throughout the home, every detail has been carefully considered to create a space that is both inviting and functional. Whether you're looking for a full-time residence or a low-maintenance luxury home in one of Central Florida's premier communities, this exceptional Winter Park property delivers style, quality, and an unbeatable location.

531 W Swoope Avenue, Winter Park
$499,900
3 Beds ⋅ 2 Baths ⋅ Flamingo Shores SubDv. ⋅ 32789 Zip Code
Welcome to your ideal single-story retreat in the heart of Winter Park's highly desirable Flamingo Shores neighborhood in zip 32789. This classic ranch-style home offers 1,979 square feet of thoughtfully designed living space, combining timeless mid-century character with everyday comfort in one of Central Florida's most sought-after locations. Designed for effortless living, the home's spacious single-level floor plan provides nearly 2,000 square feet of functional space with no stairs to navigate. At the center of the home, inviting living and gathering areas are anchored by a charming built-in fireplace, creating a warm and welcoming atmosphere for relaxing evenings or entertaining family and friends. Year-round comfort is ensured with central electric air conditioning and a reliable forced-air heating system. At the same time, public water and sewer service through the City of Winter Park provide dependable, low-maintenance utilities. Best of all, there are no HOA fees or restrictions, giving you the freedom to enjoy your property without additional regulations or monthly dues. Situated on a generous 0.26-acre lot, the home offers ample outdoor space for gardening, recreation, or future enhancements. Its exceptional location places you just minutes from the renowned dining, shopping, parks, and cultural attractions of downtown Winter Park.

351 Starling Road, Winter Park
$2,390,000
4 Beds ⋅ 5 Baths ⋅ Villa View Park SubDv. ⋅ 32789 Zip Code
Custom-built Santa Barbara-style estate set on one of Winter Park's most coveted brick-paved streets, just moments from Park Avenue's boutiques, galleries and celebrated restaurants, Winter Park Golf Course, Winter Park Racquet Club, historic Rollins College and vibrant Winter Park Village. Built in 2010, this four-bedroom, 4.5-bath residence spans 3,661 square feet across two floors, with cathedral ceilings, a cozy fireplace and colonial windows and French doors, which frame the resort-style pool retreat. A gracious main-floor primary suite offers dual vanities and a large walk-in closet. The double-island chef's kitchen features a gas range and premium Thermador appliances, anchoring an open-plan living, dining and kitchen design, modeled for everyday ease and effortless entertaining. A flexible bonus space is ideal for a home office, formal dining or gym. Upstairs, three additional spacious bedrooms each offer their own en-suite bath and walk-in closet. The home wraps around a covered courtyard leading to the heated saltwater pool and spa, creating a private outdoor enclave. Parking is a breeze with an oversized two-car garage, additional golf cart parking, plus utility pad. Ample storage and workspace complete the rear of the property, which is also wired for a future whole-home generator. A rare offering in the heart of Winter Park, where timeless design meets an unmatched lifestyle.

645 Pansy Avenue, Winter Park
$4,750,000
5 Beds ⋅ 6 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code
There are luxury homes, and then there are homes that redefine luxury altogether. Crafted by renowned luxury builder Vimaro Homes, this extraordinary residence is the product of meticulous vision, extraordinary craftsmanship, and an unwavering commitment to quality. Every space has been curated to create one of the most refined and meticulously executed homes to ever come to market in Winter Park. Situated on an expansive 15,000-square-foot homesite in the coveted Park Grove neighborhood, just moments from the boutiques and acclaimed dining of Park Avenue, the home immediately captivates with its striking architectural presence and a sweeping double-entry driveway. Beyond the front doors, a breathtaking foyer unfolds beneath soaring 22-foot ceilings, where an elegant, curved staircase, intricate marble mosaic flooring, oversized windows, and meticulous millwork establish a level of craftsmanship rarely found in today's market. Chevron-pattern engineered hardwood flooring extends throughout, complemented by exquisite natural marble and thoughtfully curated designer finishes at every turn. Designed to impress while remaining effortlessly livable, the grand living room features illuminated tray ceilings, a custom-built entertainment wall, and a sleek electric fireplace. The chef's kitchen is a true showpiece, anchored by dramatic Calacatta Viola marble countertops and backsplash, a complete Thermador appliance suite with paneled refrigerator and freezer, and a stunning ILVE range. An expansive butler's pantry with a second sink, double oven, warming drawer, dishwasher, and abundant preparation space elevates both entertaining and everyday functionality, while formal and casual dining spaces provide the perfect setting for gatherings of any scale. The primary suite is a private sanctuary designed for ultimate comfort, featuring its own coffee bar, an extraordinary custom dressing room. The primary also features a spa-caliber bath appointed with striking marble finishes, a dramatic illuminated walk-in shower, freestanding soaking tub, and Perrin & Rowe fixtures. A first-floor guest suite or dedicated office offers exceptional flexibility, while upstairs, three spacious en-suite bedrooms with walk-in closets are complemented by a hidden bonus room. Pocketing glass doors create a seamless transition to an exceptional outdoor retreat complete with a covered lanai featuring retractable screens, a fully equipped summer kitchen, resort-style pool and spa, expansive backyard, and professionally curated landscaping. Located just minutes from Park Avenue and surrounded by top-rated schools, this residence is more than a luxury home, it is a statement of artistry, craftsmanship, and timeless design that redefines what luxury new construction can be in Winter Park.

1525 Granville Drive, Winter Park
$2,299,000
5 Beds ⋅ 5 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
Under Construction. Experience modern luxury in this exceptional new construction residence by LUIH Luxury Homes, scheduled for completion in December 2026.Offering 5 bedrooms, 5 bathrooms, and 2,868 square feet of thoughtfully designed living space, this home showcases contemporary architecture, refined finishes, and a functional layout tailored to today's lifestyle. A light-filled open floor plan creates effortless flow between the living, dining, and kitchen spaces, making the home equally suited for everyday living and entertaining. Designer details and carefully selected finishes bring warmth and sophistication throughout, while expansive windows enhance the bright, inviting interiors. The private outdoor living area is designed to embrace Florida living, featuring a resort-style pool and spa with plenty of space to relax, dine, and entertain. Ideally situated near Park Avenue, residents will enjoy convenient access to boutique shopping, acclaimed restaurants, golf courses, parks, and Winter Park's renowned arts and cultural destinations, all while enjoying the comfort and quality of a brand-new luxury home.

1840 Laurel Road, Winter Park
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